18. Explore the Art Institute of Chicago
What is it?
A world-class museum guarded by its iconic bronze lions.
Why go?
With more than 300,000 works spanning centuries, the Art Institute houses masterpieces like Georges Seurat’s A Sunday on La Grande Jatte and celebrated Impressionist and modern works.
Don’t miss:
Special exhibitions highlighting masters such as Gustave Caillebotte.
19. Find Tranquility at Garfield Park Conservatory
What is it?
A stunning glass conservatory filled with more than 100,000 plants.
Why go?
Escape winter chills (or summer heat) inside lush indoor gardens. Explore the towering Palm House, desert landscapes and prehistoric fern displays—all without leaving the city.
Don’t miss:
Seasonal coffee pop-ups and rotating plant exhibitions in Horticulture Hall.
20. Score a Table at Pizz’amici
What is it?
A cozy Italian eatery famous for next-level tavern-style pizza.
Why go?
Located inside a former barber shop, Pizz’amici has quickly become one of Chicago’s most coveted reservations thanks to its perfectly crisp pies.
Don’t miss:
Grab cocktails and live music nearby while you wait for your table.
21. Laugh Out Loud at The Second City
What is it?
Chicago’s legendary comedy theater.
Why go?
Comedy giants like Bill Murray and Tina Fey sharpened their skills here before becoming household names. The mainstage revue delivers sharp, topical sketches that keep audiences roaring.
Don’t miss:
Sign up for improv classes at the Second City Training Center.
22. Visit Lincoln Park Zoo (For Free!)
What is it?
One of the last free zoos in America.
Why go?
Meet more than 1,000 animals—from lions and otters to penguins and reptiles—without spending a dime.
Don’t miss:
ZooLights, the dazzling annual holiday light display.
23. Take in the View at Willis Tower Skydeck
What is it?
An observation deck on the 103rd floor of one of America’s tallest skyscrapers.
Why go?
On clear days, you can see up to four states. Step onto The Ledge—glass boxes extending 1,353 feet above the ground—for a heart-pounding photo op.
Don’t miss:
Sunset visits for golden skyline views.
